STRUCTURAL MODIFICATIONOF 2-METHYL-2,3-DIHYDROIMIDAZO[2,1-B][1,3] TIAZOL-5(6Н)-ONE
DOI:
https://doi.org/10.32782/pcsd-2021-2-6Keywords:
2-methyl-2,3-dihydroimidazo[2,1-b][1,3]thiazol-5(6H)-one, cyclization, Knevenagel condensation, 2-methyl-6-(3-arylalylidene)-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-onesAbstract
The work is devoted to the synthesis of previously unknown 2-methyl-6-(3-arylalylidene)-2,3-dihydroimidazo[2,1-b] thiazol-5(6H)-ones. To obtain derivatives of 2-methyl-6-(3-arylalylidene)-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-ones as a starting compound used 2-methylimidazo[2,1-b]thiazole, which is obtained by cyclization of 3-allyl-2-thiohydantoin under the action of polyphosphoric acid with a yield of 93%. Condensation of 2-methyl-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-one with cinnamic aldehydes gave the target products: (Z)-2-methyl-6-{(Z, E)-3-phenylallylidene}-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-one in 85% yield, (Z)-6-{(Z, E)-3-(4-fluorophenyl) allylidene}-2-methyl-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-one in 82% yield and (Z)-6-{(Z, E)-3-(4-(dimethylamino)phenyl)allylidene}-2-methyl-2,3-dihydroimidazo[2,1-b]thiazol-5(6H)-one in 79% yield. The composition and structure of the obtained 6-arylidene derivatives of imidazo[2,1-b]thiazole were reliably confirmed by complex physicochemical analysis. In particular, NMR data of 1H- and 13C-spectroscopy, chromato-mass spectrometry, as well as elemental analysis data.
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